4-methyl-3,6-di-O-methyl-α-mangostin | 1285705-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-methyl-3,6-di-O-methyl-α-mangostin
• 英文别名: 4-Methyl-3,6-di-O-methyl-alpha-mangostin；1-hydroxy-3,6,7-trimethoxy-4-methyl-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
• CAS: 1285705-91-0
• 化学式: C₂₇H₃₂O₆
• 分子量: 452.547
• InChiKey: MABUETXAZCIAOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  α-倒捻子素 、 碘甲烷 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以14.7%的产率得到4-methyl-3,6-di-O-methyl-α-mangostin
  参考文献：
  名称：

  Cytotoxic and NF-κB Inhibitory Constituents of the Stems of Cratoxylum cochinchinense and Their Semisynthetic Analogues

  摘要：

  A new caged xanthone (1), a new prenylxanthone (2), seven known xanthones, and a known sterol glucoside were isolated from the stems of Cratoxylum cochinchinense, collected in Vietnam. Compounds 1 and 2 were determined structurally by analysis of their spectroscopic data. In addition, five new (10 and 16-19) and eight known prenylated xanthone derivatives were synthesized from the known compounds a-mangostin (3) and cochinchinone A (6). Several of these substances were found to be cytotoxic toward HT-29 human colon cancer cells, with the most potent being 3,6-di-O-acetyl-alpha-mangostin (8, ED50, 1.01 mu M), which was tested further in an in vivo hollow fiber assay, but found to be inactive at the highest dose used (20 mg/kg; ip). Of the substances evaluated in a NF-kappa B p65 inhibition assay, 1,3,7-trihydroxy-2,4-diisoprenylxanthone (5) exhibited the most potent activity (IC50, 2.9 mu M). In a mitochondrial transmembrane potential assay, two new compounds, 1 (IC50, 3.3 mu M) and 10 (IC50, 1.4 mu M), and two known compounds, 3 (alpha-mangostin, IC50, 0.2 mu M) and 11 (3,6-di-O-methyl-alpha-mangostin, IC50, 0.9 mu M), were active. A preliminary analogue development study showed that 3,6-diacetylation and 6-benzoylation both slightly increased the cytotoxicity of a.-mangostin (3), whereas methylation reduced such activity. In contrast, neither acetylation, benzoylation, nor methylation enhanced the cytotoxicity of cochinchinone A (6).

  DOI：

  10.1021/np200051j

文献信息

• Cytotoxic and NF-κB Inhibitory Constituents of the Stems of <i>Cratoxylum cochinchinense</i> and Their Semisynthetic Analogues
  作者：Yulin Ren、Susan Matthew、Daniel D. Lantvit、Tran Ngoc Ninh、Heebyung Chai、James R. Fuchs、Djaja D. Soejarto、Esperanza J. Carcache de Blanco、Steven M. Swanson、A. Douglas Kinghorn

  DOI：10.1021/np200051j

  日期：2011.5.27

  A new caged xanthone (1), a new prenylxanthone (2), seven known xanthones, and a known sterol glucoside were isolated from the stems of Cratoxylum cochinchinense, collected in Vietnam. Compounds 1 and 2 were determined structurally by analysis of their spectroscopic data. In addition, five new (10 and 16-19) and eight known prenylated xanthone derivatives were synthesized from the known compounds a-mangostin (3) and cochinchinone A (6). Several of these substances were found to be cytotoxic toward HT-29 human colon cancer cells, with the most potent being 3,6-di-O-acetyl-alpha-mangostin (8, ED50, 1.01 mu M), which was tested further in an in vivo hollow fiber assay, but found to be inactive at the highest dose used (20 mg/kg; ip). Of the substances evaluated in a NF-kappa B p65 inhibition assay, 1,3,7-trihydroxy-2,4-diisoprenylxanthone (5) exhibited the most potent activity (IC50, 2.9 mu M). In a mitochondrial transmembrane potential assay, two new compounds, 1 (IC50, 3.3 mu M) and 10 (IC50, 1.4 mu M), and two known compounds, 3 (alpha-mangostin, IC50, 0.2 mu M) and 11 (3,6-di-O-methyl-alpha-mangostin, IC50, 0.9 mu M), were active. A preliminary analogue development study showed that 3,6-diacetylation and 6-benzoylation both slightly increased the cytotoxicity of a.-mangostin (3), whereas methylation reduced such activity. In contrast, neither acetylation, benzoylation, nor methylation enhanced the cytotoxicity of cochinchinone A (6).